Antibacterial compounds containing guanidyl group

Abstract

Novel dimethylpolysiloxane compounds having antibacterial activity are disclosed. Biguanidyl group or cyanoguanidyl group are introduced into dimetylpolysiloxane compounds.

What we claim is: 
     
       1. Organopolysiloxane compounds represented by the formula (I):   R.sup.1 (Si(CH.sub.3).sub.2 O).sub.2 O).sub.1.sup.1 (Si(CH.sub.3).sub.2)AG     wherein R 1  is unsubstituted or substituted lower alkyl group, 1 is an integer of 1-5000, A is C 1  -C 10  alkylene, and G is a biguanidyl group which may have a substituent or cyanoguanidyl group; or by formula (II):     R.sup.1 (Si(CH.sub.3).sub.2 O).sub.1 (SiCH.sub.3 R.sup.2 O).sub.m (SiCH.sub.3 AG).sub.n (Si(CH.sub.3).sub.3     wherein R 1 , l, A and G are as defined above, m is an integer of 0-5000, R 2  is a lower aminoalkyl group, and n is an integer of 1-5000.   
     
     
       2. Process for preparation of the compound of formula (I), wherein G is biguanidyl group, which comprises reacting an organosiloxane containing a structural unit:   R.sup.1 (Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3).sub.2)AG     wherein R 1 , n, A are as defined above and G is a cyanoguanidyl group with an amine represented by formula     ZNH.sub.2     wherein Z is hydrogen, C 1  -C 20  alkyl or phenyl, which may be substituted with halogen, alkyl, fluoroalkyl or alkoxy.   
     
     
       3. Process for preparation of the compound of formula (I), wherein G is a cyanoguanidyl group, which comprises reacting an organosiloxane containing a structural unit:   R.sup.1 (Si(CH.sub.3).sub.2 O).sub.1 (Si(CH.sub.3).sub.2)AQ     wherein R 1  is an unsubstituted or substituted lower alkyl group, 1 is an integer 1-5000, A is a C 1  -C 10  alkylene group and Q is an amino group, with a compound NC--N═C(SCH 3 )NH 2  or NaN(CN) 2 .   
     
     
       4. Process for preparation of the compound of formula (II):   R.sup.1 (Si(CH.sub.3).sub.2 O).sub.1 (SiCH.sub.3 R.sup.2 O).sub.m (SiCH.sub.3 AG).sub.n (Si(CH.sub.3).sub.3     wherein R 1 , l, A are as defined above, G is a cyanoguanidyl, m is an integer of 0-5000, R 2  is a lower aminoalkyl group, and n is an integer of 1-5000, which comprises reacting a compound of formula (II):     R.sup.1 (Si(CH.sub.3).sub.2 O).sub.1 (SiCH.sub.3 R.sup.2 O).sub.m (SiCH.sub.3 AQO).sub.n (Si(CH.sub.3).sub.3     wherein the R, l, m, n nd a are the same and Q is an amino group with a compound of formula:     NC--N═(SCH.sub.3)NH.sub.2     or a compound of formula:     NaN(CN).sub.2.     
     
     
       5. Process for preparation of the compound of formula (II):   R.sup.1 (Si(CH.sub.3).sub.2 O).sub.1 (SiCH.sub.3 R.sup.2 ().sub.m (SiCH.sub.3 AGO).sub.n (Si(CH.sub.3).sub.3     wherein R 1 , l and A are as defined above, G is a biguanidyl, m is an integer of 0-5000, R 2  is a lower aminoalkyl group, and n is an integer of 1-5000, which comprises reacting a compound of formula:     R.sup.1 (Si(CH.sub.3).sub.2 O).sub.1 (SiCH.sub.3 R.sup.2 O).sub.m (SiCH.sub.3 AQO).sub.n (Si(CH.sub.3).sub.3     wherein the R, l, m, n and A as defined above and Q is an amino group with a compound of formula:     ZNH.sub.2     wherein Z is hydrogen, C 1  -C 20  alkyl, fluoroalkyl or alkoxy.